Payworks is a leading workforce management solutions provider and multi-year winner of the Canada’s Best Managed Companies program. With clients of all sizes and more than 600 employees, we currently have an exciting opportunity on our Product Management team for the right candidate.

The Product

Manager owns one or more AI-first initiatives end-to-end — from discovery, through delivery, to measured adoption — inside Payworks' payroll and HCM platform. Payworks builds regulated software for 40,000+ Canadian SMBs across all 13 provincial and territorial jurisdictions, in English and French. This role turns that compliance depth into AI-assisted products Canadian businesses trust: software that monitors, flags, and guides payroll and HR work while keeping a human in the loop on every decision that carries regulatory weight.

The Product

Manager works as an individual contributor inside our AI Product Development Lifecycle (AI PDLC), building working prototypes, sequencing delivery into valuable increments that our design partners help shape along the way, and shipping each release with the telemetry to prove it changed a user outcome. This role stays ahead of the development team at all times. Comprehensive employer paid benefits, including a Health Spending Account, for you and your family and excellent pension plan with employer contributions.

Plenty of professional development opportunities. Community-minded culture – Receive two paid days per year to volunteer and lots of opportunity to “Pay it Forward”. Time and flexibility to meet your needs – Hybrid work model with versatile work options, plus 3 weeks vacation to start, flex time and parental leave benefits.

Cool perks – Annual Lifestyle Spending Account, fun office environment and events, and more! You'll design the confidence signals, review steps and accuracy history that move a payroll practitioner from watching the AI to relying on it. Keep the pipeline ahead of the team – You'll break the work into small,



well‑specified pieces and stay a step ahead of engineering, partnering closely with Business Analysts and developers so they can build straight from your prototype.

Prove it worked – Every release ships with the measures built in to show whether it changed a real outcome, and every roadmap item traces back to one. You'll work with Sales, Marketing, Support, Implementation and Finance on positioning, launch materials, and the case for why clients should trust it. 5–8 years in B2B SaaS product management, including products you shipped that measurably changed something for users or the business. ~ Sharp discovery and delivery instincts: you prioritize by risk rather than convenience, and you're happy working from prototypes and shared context instead of requirement documents. ~ Comfort with measurement: you instrument what you ship and tell leading indicators from lagging. ~ Sound judgment in ambiguity, and the ownership to carry deliverables, timelines and quality through every release. ~ Clear, declarative writing in English, and a collaborative style that treats other teams as co‑creators rather than requesters. ~ Considered an asset: Canadian payroll or HCM experience, or product work in another regulated space like fintech, health, insurance or security. You've shipped an AI or ML product in production, including work on quality, evaluation or trust design.

Comfort working in French, since we serve clients and meet payroll compliance requirements in both official languages (EN/FR). We are proud to support a Flexible Work Plan that recognizes the diverse needs and lifestyles of our people.

The Product

Manager has the option to work fully from the Payworks office in Winnipeg or on a hybrid work model, working in the office at least three (3) days a week. Some travel may be required. Individuals applying for employment with Payworks may request accommodations at all stages of recruitment and employment from Human Resources. Payworks does not use artificial intelligence (AI) technologies in the screening, assessment, or selection of applicants at any stage of the hiring process.

📌 Product Marketing Manager - Commercial (Remote) (Winnipeg)
🏢 Payworks
📍 Winnipeg